Water → HCID 86707751, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-5-[(4-chloro-2-methyl-phenyl)-hydroxy-methyl]-1-isopropyl-1H-imidazole-4-carboxylic acid ethyl ester (intermediate C, 3.5 g, 8.4 mmol) in dioxane (80 ml)/H2O (20 ml) were added 2-methoxy-phenyl boronic acid (2.0 g, 13.2 mmol), K2CO3 (3 g, 21.7 mmol). The mixture was degassed for 5 min and then Pd(PPh3)4 (1.7 g, 1.5 mmol) was added. The mixture was stirred at 100° C. for 2 h to give a complete conversion. Dioxane was removed under reduced pressure. The residual material was dissolved in EtOAc and extracted with brine. The aqueous layer was washed with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The product was fixed on silica gel and purified by flash chromatography (silica gel, solvent: CH2Cl2/EtOAc, 100:0→80:20) to give the title compound as a yellow foam. tR: 1.27 min (LC-MS 2); ESI-MS 433.3 [M+H]+ (LC-MS 2). 1H-NMR (DMSO-d6, 400 MHz) δ ppm 7.56-7.48 (m, 2H), 7.29-7.05 (m, 3H), 7.34-7.29 (m, 1H), 7.10-7.96 (m, 1H), 6.94-6.91 (m, 1H), 6.52 (d, 1H), 4.58-4.52 (m, 1H), 4.24 (q, 2H), 3.73/3.68 (s, 3H), 2.16 (s, 3H), 1.27 (t, 3H), 1.05 (d, 3H), 0.58 (d, 3H).

Provenance & Evidence